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I haven’t written any updates lately because there’s been little to write about. Most of my activities with my wife and Mistress have been curtailed due to issues with post-surgical healing. But things are looking up.

My first 6-7 weeks post-op went quite well. Minimal pain, considering that this was major surgery. But then things started to hurt, and hurt more. For various reasons I wasn’t able to get the medical attention I needed until last week. And even then things aren’t 100% resolved yet.

So, unfortunately, The Drawer still remains unused for it’s intended purpose. Mistress has talked about it recently, though. I’m hoping to post a few pictures of the D-rings that I mounted in The Drawer for eventual restraining uses.

I specifically asked my doctor about resuming anal sex, and she was fine with it. Since then, Mistress has made it clear that she intends to go there sometime soon. Not sure what she has in mind, stay tuned.

And for more updates about how my Gender Confirmation Surgery is really going, see my other blog “Blooming Time”.

Mistress gets to make the rules. She also can change the rules. And that’s just what she did.

I’d been working hard on her business taxes, spending many many hours. She decided that (plus my work on our personal taxes) was worthy of a reward.

“When you finish the taxes,” she told me a few days ago “then I will let you cum inside me – without the four-day rule.” This was incredible news!

As I wrote in a recent post, she had decided that I must be nice and not grumpy for four days after intercourse with her, or else she would never let tiny (her name for my cock) inside her again. To earn an exception to her ultimatum was really something.

So last night I claimed my orgasm inside her. I didn’t stress about it, we just got busy with it at bedtime (when she normally would have me just pleasure her with my hand or mouth). About halfway through she seriously stimulated my nipples, which brought me over the edge in a hurry. It had been just over 3 weeks since my last orgasm.

While it was very nice, I found myself a bit disappointed. In some other recent posts I’ve discussed the “female orgasms” that I have experienced recently, with her help. This “male orgasm” felt, well, shallow in comparison. It was intense, but brief, and physically limited to tiny. Pretty quickly afterwards I was back to normal (no afterglow).

Of course, all I’ve ever known my whole life is the penis-based orgasm. But now that I’m working toward transitioning into a female, I’m finding out so many interesting things. Like how ready my body and brain was to experience a non-penis-based orgasm. And how my body responded in a very recognizably female way.

Anyway, tiny is locked back up. Despite the bulk of the cage, I can still crossdress quite effectively. Mistress sent me out shopping dressed in a pink top, some cute flats, cropped pants, and some nice jewelry. I added a little makeup too, mostly to cover my facial hair, but some eye treatment too. We both feel I look really good, and I’m not aware of anyone noticing me at all. It feels good to pass as a woman.

This coming week is busy. I’m seeing my gender transition therapist for the 2nd time. We’ll be talking about the plan and schedule from here. I hope to finally hear something definite about hormones. And later in the week I have my first laser hair removal appointment for my face. Progress!

Mistress has been using me as her urinal sometimes at bedtime. She’s getting to like how it saves her a trip to the other end of the house into a cold bathroom. I’m just loving serving her and making her happy.

I have a new blog page partway completed. It will be focused on accomplishing affordable, inescapable male chastity as we have. I’ll have more pictures, information about prices, and extra details that were not in my previous article. I hope to publish it in the next few weeks.

“Make your tiny cock hard, and rub it against my clit. I want an orgasm,” my wife and Mistress said.

This would be as close as I’ve been to being inside her for over two months. The prospect of feeling her warm, soft pussy lips against my unlocked cock was going to be quite a treat for me. Just imagining how the moistness of her labia would feel against the head of my cock made me quickly get hard for her.

I guess being out of my chastity cage for a week (while it gets resized) has more benefits than I realized.

She pulled the bed covers down, revealing her unclothed bottom half. Slowly she bent her knees and separated them, revealing her genitals to me so seductively. As I moved into position, she pulled her glistening pussy lips apart, revealing her sensitive nub that apparently needed some attention.

I lowered myself and gently put my cock head against her opening. She startled – apparently my PA ring was cold. Damn. “I don’t want that ring there; slide up further,” she directed. I did so, and my cock head approached her belly button. My shaft pressed against her clit now, and she started enjoying the pressure.

She began to grind herself against me, and I realized that this position gave me basically no glans stimulation at all. So I redirected my attention to ensuring that her pleasure was uninterrupted. It didn’t take her long to climax, after which I snuggled in and just hugged her as she floated in that post-orgasmic state.

Eventually she opened her eyes, smiled, and asked “I suppose you’d like to go inside me?”. I responded “Of course,” fully expecting her to decline as part of her ongoing teasing. She said “Well, it’s probably going to be a hassle to remove that ring, you probably need some tool from downstairs…” She likes to leverage any excuse to deny me.

“Actually, Mistress, the tool happens to be right here on the dresser,” I said. I could tell by her smirk that she was amused that I had anticipated this possibility. Even so, I expected only to be taunted further. Just because I’m unlocked from chastity for a few days doesn’t mean she would allow me to have intercourse with her. I briefly fantasized about being allowed to just rub my cock head against her now very wet pussy lips for a minute or two, and then she’d roll over and go to sleep.

Which is why I was shocked when she said “Ok, take it [the ring] out.” I quickly removed the 8 gauge ring from my pierced cock and rejoined her on the bed. Just to be sure, I asked: “Mistress, please may I cum inside you?” I couldn’t believe it when she agreed. Despite his lack of use, tiny (her name for my cock) remained hard enough for me to slip inside her wonderful, warm, wet, snug, delicious pussy.

It had been well over two months since she had last permitted this. As a result, the intensity of the sensation was very high, and it didn’t take me long at all to orgasm. It’s good that she had hers first, because I I don’t think I could have lasted long enough to bring her over the edge. It was so incredible to feel her vagina hugging tiny again. I felt extremely grateful to have been allowed that pleasure.

As we chatted afterwards, I got the impression that she was going to want more intercourse going forward. She wanted that pleasure for herself. I’m not sure how that’s going to work when, probably early next week, I’ll be locked back into chastity. Taking my captive bead PA ring out is super easy. Removing the PA lock and the JailBird is nowhere near as quick. But I guess that’s my problem, not hers, right?

Of course I’m also assuming that she meant more intercourse with me. Although she teases me a lot and talks about sex with other men often, I don’t think she’s serious about actually doing it. Sometimes I think I must be crazy to want that and to be locked up for months myself, instead of having sex with her myself.

Having experienced a little serious chastity and denial, I find myself drawn deeper into it. During these days of being unlocked, I find myself a bit uncomfortable about having free access to my cock. I’ve even urinated standing up a few times, and it feels like I’m getting away with something. It’s as if something in me has switched over to chastity as the norm for me now.

In related news, I completed a modification to the PA lock. There was a part of the brass locking cylinder that stuck out. The corners of that little metal piece would poke into my scrotum providing wincing-level bad pain on occasion. It turned out to be quite easy to file down that piece and round the remaining edges. It doesn’t diminish the lock security in any way, and it should be much more comfortable.

I actually am really looking forward to getting locked back into my resized JailBird. I sent it back to have the base ring enlarged. The problem was that when Mistress would get me seriously aroused, that base ring would get so tight I could barely stand it. Because the PA-lock prevents pull-out, a larger base ring isn’t a security concern.

I expect that the new base ring and increased lock comfort will allow me to wear the JailBird continuously for weeks or months. Whatever Mistress wants.